The Transsexual Who Surpassed All My Fantasies

After what happened with Mónica in Seville, I thought I’d be able to forget it in time. That it had been a one-off experience, the result of an exceptional night and my wife’s presence, and that the memory would gradually lose strength, as usually happens.

I was wrong.

Fourteen months had passed and there were still nights when I remembered her with disconcerting clarity: her voice, deep and soft at the same time, the way she moved around that vacation rental apartment, and the way the three of us had ended up at that point without any of us having fully planned it. It was something that happened with a naturalness none of us expected.

My wife —Paula— never wanted to repeat it. She didn’t say so directly, but every time I brought up the subject she changed the conversation with that skill of hers, never closing doors, just diverting traffic. I understood the message without needing translation. For her, once was enough. For me it was different. For me Mónica had opened something I had no interest in closing.

The problem was the standard. I had been browsing contact sites irregularly for months, without finding anything that quite convinced me. Too artificial, too obvious, too distant. What made Mónica special was not just her body, but a certain way of being present that was hard to find.

Until one afternoon I came across Valentina’s ad.

The photo showed a woman with dark brown hair pulled into a loose bun, narrow shoulders and generous hips. She wore a tight black dress and looked straight at the camera with an expression that mixed confidence and something hard to define: invitation, perhaps, without urgency. She wasn’t Mónica. But something in that image made me keep staring longer than necessary.

Paula was spending the weekend at her parents’ house with the kids. The house was mine.

I called without giving myself any more time to think about it.

Valentina answered on the second ring. Her voice was more feminine than I’d expected, clear and direct, with a slight accent I couldn’t quite place. I told her I’d seen her ad. She asked me three brief, specific questions, no beating around the bush, and before hanging up she added something I wasn’t expecting:

—Come unhurried. Rushing ruins good afternoons.

I laughed. We agreed on the time.

***

I showered without hurrying, shaved, chose comfortable clothes. As I locked the front door behind me I wondered, as always in these situations, whether I was making the right decision. The answer was yes, with the same calm certainty that comes over me when I know something is what I want.

The address took me to an old building on a narrow street in the center, the kind with uneven cobblestones and balconies with flowerpots. I climbed to the third floor by a stone staircase that smelled of old wood and rang the bell. While I waited, I realized my hands were slightly tense.

The door opened and I had to readjust all my expectations.

Valentina was shorter than the photo suggested. Not by much, but enough for the first impression to be different from the image I’d built in my head. She wore the same black dress from the pictures, fitted to curves that might have looked edited in the photo and were completely real in person. Her dark brown hair, loose now, reached her shoulders. She had gray-green eyes with a way of looking that was direct without being aggressive.

—You must be Roberto —she said.

—The one and only —I managed to answer.

She kissed me on both cheeks, as if we already knew each other, and gestured for me to come in.

The apartment was small but had personality: a wooden bookshelf with neatly arranged books, a plant on the windowsill, a floor lamp in a corner casting a warm orange light. A blue armchair by the window. It wasn’t what I had imagined when I dialed her number.

—Do you prefer wine or something stronger? —she asked from the kitchen.

—Wine, thanks.

I stood looking at the book titles. I recognized a couple and pointed them out when she came back with the glasses. That sparked a conversation that lasted almost twenty minutes without either of us seeming in any hurry. Valentina really listened, asked sensible questions, answered with judgment. There was something about that natural ease that disarmed me more than anything she might have done deliberately to break the ice.

At some point I realized I’d spent several minutes looking at her mouth while she talked.

—Do you have any preferences? —she asked at one point, with the same calm she might have used to ask whether I wanted more wine.

—I’d rather we just let things happen —I replied.

Valentina set her glass on the side table, stood up, came over to me and kissed me on the neck. Softly, without urgency. Her hands found the buttons of my shirt.

***

She didn’t do it quickly. Button by button, with a quiet concentration that made every second carry its own weight. When the shirt hit the floor, she gently pushed me back against the sofa and knelt in front of me, between my open legs, her eyes fixed on the bulge already straining the fabric of my pants.

She didn’t take my pants off right away. Her hands worked first over the fabric, following the outline of my hard cock, squeezing it through the cloth with measured pressure that made me close my eyes without realizing it. Then she lowered her face and bit it softly over my clothes, mouth open, breathing hot against the fabric until the dampness of her saliva started to mark it. She knew exactly where to go and how long to linger in each place.

When she finally opened my pants and yanked my underwear down, my cock sprang upward and brushed her lips. She gripped it at the base with her right hand, lifted her gaze to me for a second —those gray-green eyes, calm, waiting— and without looking away stuck out her tongue and licked me from my balls to the tip, with a deliberate slowness that tore a rough groan from me.

—I’m going to suck your cock slowly —she said—. Take it.

And she took it all into her mouth.

I felt the head hit the back of her throat and stay there, her swallowing around it, without pulling away. Then she started moving up and down with a tight rhythm, pressing her lips together, flattening her tongue against the vein that runs underneath. She pulled it from her mouth dripping with saliva, looked at me, and took it back in. She alternated: now just the tip, sucking my head like it was candy, teasing the frenulum with her tongue until my thighs trembled; now all the way to the base, with her nose pressed to my pubic mound and one hand stroking my balls with the pads of her fingers.

Every time I was about to come, she could sense it by the way my belly tightened, eased off the pressure, pulled my cock out of her mouth and held it in her hand, giving little licks to the swollen head until the urgency dropped a notch. Then she’d start again. She kept me like that, on the edge, longer than I thought a man could possibly last without cumming. I could see her chin shining with saliva, fine strings hanging from my cock to her lips, and that calm gaze that never left mine.

When she pulled away, she stood up and kissed me on the mouth. I could taste the mix of us, the salty flavor of my own arousal on her tongue.

Then she stepped back and started taking off her dress.

She didn’t do that quickly either. She lifted it slowly over her hips, turning at just the right moment to give me her back, so that what I saw first was the curve of her ass framed by a black lace thong that disappeared between her cheeks. The dress kept rising. The fabric passed over her waist, over her back, and when it was at her ankles she turned toward me.

The sight I found there left me completely still.

Her tits were big, round, firm in a way that challenged my expectations of what was possible, capped by dark nipples already hard. But that wasn’t what took my breath away. It was the contrast: that body of feminine curves, the narrow waist, the broad hips, the soft thighs, and between her legs, pushing the thin fabric of the thong forward, the unmistakable evidence of a completely hard cock. She pulled the thong down with both hands and her shaft sprang upward, thick, the head shiny and the veins standing out. Her whole body, small and generous, with that stiff cock pointed at me, made me hotter than anything else I’d seen in a long time.

I stood up from the sofa without thinking. I knelt in front of her.

Valentina let out a sound when I took her into my mouth. Not an exaggerated or theatrical moan, but something much more restrained and real, a low gasp that came from her chest. Her cock felt heavy on my tongue, hot, with a pulse of its own that I could feel against my palate. I had never sucked a cock before, and yet I went right into it, closing my lips around the shaft and taking it as far down as I could, learning its shape with my tongue, squeezing my cheeks to create suction as I came back up.

—Like that —she murmured—. Easy. Suck it like that.

Her hands found my hair without gripping, simply keeping pace with the rhythm I set. I dared to do more: I licked her from the balls, going up the thick vein that ran along the shaft, until I closed my lips over the head and took her back down again. Saliva dripped from my chin. I held her balls in my palm and stroked her perineum with my thumb. She closed her eyes, threw her head back, and I could feel her cock swelling even more in my mouth. I could sense how she controlled her breathing more and more with effort, how a tremor ran through her thighs.

When I pulled away, both of us were breathing hard and her cock was shining with my saliva, pointed at my face.

—I want you to fuck me —I said.

Valentina looked at me with that calm expression she’d had since she opened the door.

—Slowly —she replied—. I’m going to take it all the way in, but at my pace.

***

I lay on my back at the edge of the sofa with my knees pulled up to my chest, offering her my open ass. Valentina took a bottle of lube from the side table drawer, squeezed some onto her fingers, and ran them over my asshole, drawing slow circles until the entrance began to give. She slipped in one finger first, all the way, moving it slowly. Then two, gently scissoring them to stretch me. I tightened and loosened around her fingers, feeling my own body opening to her. There was no urgency in any of her movements. That, in itself, was part of what made everything work.

She lubed her cock with her other hand, coating it from top to bottom until it gleamed. Then she gripped it by the base and pressed the head to my asshole. When I felt the tip pushing at my entrance, I instinctively tensed.

—Breathe —she said—. Let the air out when it goes in.

I took a deep breath and let it out slowly.

The head pushed through with a dull tug. Valentina stayed still, letting me take in the stretch, and then pushed another centimeter. And another. She pushed, waited, watched my face, adjusted the pressure according to what she read in my expression. The initial pain was brief, an acute prelude that dissolved almost immediately into something completely different: a deep, hot fullness that climbed up my spine. When I felt her enter all the way, with her balls resting against my ass cheeks, the effect was immediate. An internal pressure that changed the whole landscape of sensation and had my cock dripping against my belly without anyone touching it.

She stayed still for a moment, looking at me, her cock buried all the way in and throbbing inside me.

—Good? —she asked.

—More than good —I answered. And it was true.

She started moving. A slow rhythm at first, almost pulling out completely before plunging back into me to the base, the tip brushing something deep that made me moan every time she hit it. She gradually built momentum. My ass began to slap against her pelvis, a wet, rhythmic sound filling the living room. With one hand she held me behind the knee, bending me more to take her deeper; with the other she took my cock and started jerking me in time with her thrusts.

—You love it —she whispered, never stopping—. Look at you. You’re drooling because you’ve got my cock inside you.

—Yes —I managed to say—. Harder. Fuck me harder.

And she fucked me harder. She sped up her hips, driving it in with dry, sharp thrusts that pulled grunts out of me, never stopping her hand working my cock. The combination was devastating: the pressure of the cock hammering inside me, searching for that point that made me see lights, and the friction of her fingers clamped around my head. I closed my eyes. I opened them. I wanted to see her face.

Valentina looked at me while she destroyed me. Her tits bounced with every thrust, her nipples hard, her hair falling over her face, her mouth slightly open. That gaze, direct and unbroken, was almost as intense as the cock she was driving into me all the way.

I tried to hold out. I couldn’t.

I came with a force that tore a sound from me I didn’t recognize as my own. I shot in thick, long spurts, spilling over my belly and chest while Valentina kept moving without stopping, squeezing my cock just below the head to wring out the last drop. The orgasm came in overlapping waves, one after another, each thrust of hers extending each wave until I was completely spent and left motionless, my muscles slack, my belly slick with semen and my ass still split open by her cock.

When she reached the edge herself, she pulled out of me with one firm motion, climbed onto the sofa kneeling over my torso, and stroked her cock two fingers’ width from my face. I watched her cum: the tip swelled, turned purple, and suddenly started firing hot spurts of semen that landed on my cheek, my lips, my neck, mixing with my own load on my chest. It was brief and focused, without theatrics, as real as everything that had happened that afternoon. She came with clenched teeth, with a low moan, and the last drops she flicked onto my open tongue.

Then she lay down beside me for a minute in silence, both of us sticky.

The only sound was our breathing, slowly returning to normal.

***

She helped me sit up. She went to the kitchen and came back with two glasses of water and a damp towel, which she used to wipe my chest and face with the same calm she’d shown throughout everything else. We sat on the sofa and drank in silence for a while, with that strange calm that comes after a completely resolved tension. Then we talked again, unhurriedly, about things that had nothing to do with what had just happened.

When I stood up to leave, Valentina walked me to the door with the thong on again and her hair slightly tousled, as calm as when she’d opened it.

—Next time —I said as I put on my jacket—, I want to be the one fucking you.

—I know —she cut in with a slight smile—. Next time.

I went out into the street with my legs a little unsteady and the absolute certainty that I wasn’t going to take long to come back.